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F5251

p-Fluoro-DL-phenylalanine

Name: <I>p</I>-Fluoro-<SC>DL</SC>-phenylalanine
Brand: SIGMA

≥98.0% (TLC)

Sinónimos:

4-fluoro-phenylalanine

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Fórmula lineal:

FC₆H₄CH₂CH(NH₂)COOH

Número CAS:

51-65-0

Peso molecular:

183.18

NACRES:

NA.26

PubChem Substance ID:

24894885

eCl@ss:

32160406

UNSPSC Code:

12352209

EC Number:

200-113-7

MDL number:

MFCD00002600

Beilstein/REAXYS Number:

2938793

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Propiedades

Nombre del producto

p-Fluoro-DL-phenylalanine,

assay

≥98.0% (TLC)

Quality Level

100

form

powder

color

white to off-white

mp

253-255 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

NC(Cc1ccc(F)cc1)C(O)=O

InChI

1S/C9H10FNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)

InChI key

XWHHYOYVRVGJJY-UHFFFAOYSA-N

Descripción

Biochem/physiol Actions

Inhibits mitosis and reversibly arrests HeLa cells in G2.

p-Fluoro-DL-phenylalanine (pFPhe), a toxic antimetabolite, is a racemic mixture of a substituted (halogenated) benzoyl D and L phenylalanine useful as a selection marker for wine yeast transformation and with potential use in endomorphin, antiviral, and antimicrobial drug development. Phenylalanine analogue, rho-fluorophenylalanine (pFPhe) is also used to induce apoptosis.

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Este artículo	F5126	68047	G2505
Sigma-Aldrich F5251 p-Fluoro-DL-phenylalanine	Sigma-Aldrich F5126 m-Fluoro-DL-phenylalanine	Sigma-Aldrich 68047 4-Borono-D-phenylalanine	Sigma-Aldrich G2505 N-Glutaryl-L-phenylalanine p-nitroanilide
form powder	form powder	form solid	form powder
assay ≥98.0% (TLC)	assay ≥98%	assay ≥97.0% (HPLC)	assay ≥98% (HPLC)
Quality Level 100	Quality Level -	Quality Level 100	Quality Level 100
color white to off-white	color white to off-white	color -	color -
mp 253-255 °C (dec.) (lit.)	mp 240-250 °C	mp -	mp -
application(s) peptide synthesis	application(s) cell analysis peptide synthesis	application(s) peptide synthesis	application(s) -

pictograms

GHS06

signalword

Danger

hcodes

H300

pcodes

P264 - P301 + P310

Hazard Classifications

Acute Tox. 2 Oral

Clase de almacenamiento

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Protein tyrosine kinase p56lck-deficiency confers hypersusceptibility to rho-fluorophenylalanine (pFPhe)-induced apoptosis by augmenting mitochondrial apoptotic pathway in human Jurkat T cells.

Hae Sun Park et al.

Biochemical and biophysical research communications, 377(1), 280-285 (2008-10-11)

Phenylalanine analog, rho-fluorophenylalanine (pFPhe)-mediated cytotoxicity and several apoptotic events including mitochondrial cytochrome c release, activation of caspase-9, -3, and -8, Bid cleavage, degradation of PARP and PLCgamma-1, and DNA fragmentation were more significant in p56(lck)-deficient Jurkat T cells (JCaM1.6) than

(De)regulation of key enzyme steps in the shikimate pathway and phenylalanine-specific pathway of the actinomycete Amycolatopsis methanolica.

H Kloosterman et al.

Microbiology (Reading, England), 149(Pt 11), 3321-3330 (2003-11-06)

Prephenate dehydratase (PDT), chorismate mutase (CM) and 3-deoxy-D-arabino-7-heptulosonate 7-phosphate (DAHP) synthase are key regulatory enzymes in aromatic amino acid biosynthesis in the actinomycete Amycolatopsis methanolica. Deregulated, feedback-control-resistant mutants were isolated by incubation of A. methanolica on glucose mineral agar containing

Comparison of two alternative dominant selectable markers for wine yeast transformation.

Eduardo Cebollero et al.

Applied and environmental microbiology, 70(12), 7018-7023 (2004-12-03)

Genetic improvement of industrial yeast strains is restricted by the availability of selectable transformation markers. Antibiotic resistance markers have to be avoided for public health reasons, while auxotrophy markers are generally not useful for wine yeast strain transformation because most

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SKU	GTIN
F5251-1G	04061826059326
F5251-5G	04061833618127

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p-Fluoro-DL-phenylalanine

≥98.0% (TLC)

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assay

Quality Level

form

color

mp

application(s)

SMILES string

InChI

InChI key

Biochem/physiol Actions

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Información de seguridad

pictograms

signalword

hcodes

pcodes

Hazard Classifications

Clase de almacenamiento

wgk

flash_point_f

flash_point_c

ppe

Documentación

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